Creating Content (and Connections) Fearlessly Ft. Ollie Whitfield

As the Demand Gen Team Lead at VanillaSoft, Ollie Whitfield strategizes creative ways to reach B2B companies. During our interview, he shared his takes on creating engaging content and more. 

How Did  Your Career Journey Unfold?

During his school years, Ollie Whitfield stumbled upon a social media apprenticeship role that intrigued him. Despite having limited knowledge about it, he decided to go for it. 

"I finished my last exam on a Thursday. I started work on a Monday and from there I was going from ‘You've got zero pounds and zero pennies in your bank to Oh my God, I just got paid for two weeks [of] work,’ you know, I was hooked and I made a lot of coffees. I swept a lot of floors.”

Whitfield says tasks like making coffee and sweeping floors pushed him to pursue a more substantial role. He went on to embrace opportunities beyond his qualifications in the agency setting, which would mark a turning point. With more time and more opportunities to contribute, Whitfield realized the industry was engaging and full of potential. Over the years, he progressed from a small company to a larger agency and eventually landed at VanillaSoft.

Do You Have Any Skills That Are Transferable Across Diverse Roles?

One key skill that proved transferable was sales expertise. At Whitfield’s initial company of only three people, every team member was responsible for selling. He chose to put in the effort and begin cold emailing prospects. Admittedly, Whitfield says he wasn’t as skilled at writing emails at that point in his career. He gained experience and honed the ability to succinctly communicate value in emails, making them more appealing. This skill became invaluable in various contexts, from reaching out to prospects to securing prominent podcast guests.

What Are Your Insights on Leadership and Effective Communication?

Whitfield’s most valuable leadership lessons emerged from client interactions rather than internal reporting structures. While working in an agency, he provided services while also offering advice against certain decisions. 

“I had quite a big range in personas across my client base.”

This dynamic taught him vital lessons in delivering feedback effectively and adapting a communication style based on the client's personality and where their priorities lie. 

How Do You Unleash Creativity and Apply It to Your Work?

A part of Whitfield’s creative process involves identifying aspects he finds otherwise mundane and reimagining them to be more engaging. Finding traditional webinars to be boring, Whitfield was inspired in unlikely places, like reality TV shows. This led to innovative webinar formats such as Emailing With the Stars. Whitfield advises others to infuse their unique interests into their work. 

“Do whatever suits you, so for instance if you're quite introverted and you love books, maybe there's a book that's out there that could be translated into your content.”

How Did Your Podcast Come to Be?

Starting the 0 to 5 Million Podcast was the result of a need to create fresh marketing content for his company. Alongside co-host Shawn Finder Whitfield interviews individuals running businesses from 0 to 5 million in revenue as they share their entrepreneurial journeys. The duo adopted a rule-free approach, recording episodes at varying lengths and featuring various guests all with the goal of keeping it genuine and enjoyable.

Interested in connecting with Ollie Whitfield? You can find the 0 to 5 Million Podcast on various podcast platforms. Additionally, you can connect with Ollie via LinkedIn, where he shares insights and engages with the community.